1083168-94-8|2-Methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine| Ambeed

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Quality Control of [ 1083168-94-8 ] Purity: 95% SDS Specification

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Product Details of [ 1083168-94-8 ]

CAS No. :	1083168-94-8
Formula :	C₁₂H₁₇BN₂O₅
M.W :	280.08
SMILES Code :	CC1(C)C(C)(C)OB(C2=CN=C(OC)C([N+]([O-])=O)=C2)O1
MDL No. :	MFCD12923397
InChI Key :	XWXOPFXUTOQOSM-UHFFFAOYSA-N
Pubchem ID :	57416495

Safety of [ 1083168-94-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1083168-94-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	6
Fraction Csp3	0.58
Num. rotatable bonds	3
Num. H-bond acceptors	6.0
Num. H-bond donors	0.0
Molar Refractivity	76.03
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	86.4 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.97
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.3
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.29
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.82
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.43

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.84
Solubility	0.403 mg/ml ; 0.00144 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.41
Solubility	0.109 mg/ml ; 0.000389 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.13
Solubility	0.208 mg/ml ; 0.000741 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.61 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	3.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.15

Application In Synthesis of [ 1083168-94-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1083168-94-8 ]

[ 1083168-94-8 ] Synthesis Path-Downstream 1~35

1
[ 152684-30-5 ]
[ 73183-34-3 ]
[ 1083168-94-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; for 2.0h;Reflux;	The mixture of 5-bromo-2-methoxy-3-nitropyridine (5 g, 21 .5 mmol),4,4,4',4',5,5,5',5' -octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (6.6 g, 25.8 mmol) ,PdCl2(dppf)-CH2Cl2 (500 mg) and potassium acetate (6.3 g, 64.5 mmol) in anhydrous 1 ,4-dioxane (200 ml_) was refluxed for 2h. Then the solvents were removed. The crude product was purified by chromatography on silica gel using petroleumether:EtOAc =10:1 as eluent to afford 2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)pyridine in 81 % yield (5 g). m/z 281 (M+H)+.
81%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; for 2.0h;Reflux;	The mixture of 5-bromo-2-methoxy-3-nitropyridine (5 g, 21.5 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (6.6 g, 25.8 mmol), PdCl2(dppf)-CH2Cl2 (500 mg) and potassium acetate (6.3 g, 64.5 mmol) in anhydrous 1,4-dioxane (200 mL) was refluxed for 2 h. Then the solvents were removed. The crude product was purified by chromatography on silica gel using petroleum ether:EtOAc=10:1 as eluent to afford 2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine in 81% yield (5 g). m/z 281 (M+H)+.
80%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80.0℃;	AL 2-Methoxy-3-nitro-5-(4,4,5,5-tetramethyl-L3,2-dioxaborolan-2-yl)pyridine; To a dry flask was added 5-bromo-2-methoxy-3-nitropyridine (1.3 g, 5.0 mmol),4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.6 g, 6.4 mmol), and Pd(dppf)Cl2 (0.2 g, 0.25 mmol). Potassium acetate (1.5 g, 15 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (30 mL) was added and the reaction was heated at 80 0C in an oil bath overnight. The reaction mixture was evaporated to dryness. The residue was dissolved in ethyl acetate (20 mL) and washed with water (20 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting material was purified by silica gel chromatography (eluting with 0-50% ethyl acetate in hexane) to yield the product (0.2 g, 15%). ESI-MS m/z calc. 280.12, found 199.1 (MW[-C6Hio]+l)+. Retention time 0.7 minutes.

References: [1]Patent: WO2012/34526,2012,A1 .Location in patent: Page/Page column 33.
[2]Patent: US2013/190307,2013,A1 .Location in patent: Paragraph 0158; 0159.
[3]Patent: WO2008/141119,2008,A2 .Location in patent: Page/Page column 105.
[4]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 256 - 261.
[5]Bioorganic and Medicinal Chemistry,2019,vol. 27.

2
[ 936727-68-3 ]
[ 1083168-94-8 ]
[ 1083168-26-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80.0℃;	CB. N-(6-(5-amino-6-oxo-1.6-dihvdropyridin-3-yl)-5-methylpyridin-2-yl)-l-(2 ,2-difluorobenzo FcTIf I ,31 dioxol-5 -vDcyclopropanecarboxamide; Step a: l-(2, 2-DifluorobenzofdJfl, 3Jdioxol-5-yl)-N-(6'-methoxy-3-methyl-5 '- nitro-2, 3 '-bipyridin--yljcyclopropanecarboxamide; To N-(6-chloro-5-methylpyridin-2-yl)-l-(2,2-difluorobenzo[(/][l,3]dioxol-5- yl)cyclopropanecarboxamide (0.11 g, 0.3 mmol) in 1 ,2-dimethoxyethane (3 mL) was added 2- methoxy-3-nitro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (0.11 g, 0.39 mmol), tetrakis(triphenylphosphine)palladium (0) (17 mg, 0.015 mmol), and 2 M sodium carbonate (0.3 <n="151"/>mL, 0.6 mmol) and the reaction mixture was heated to 80 0C overnight. The crude material was purified by silica gel chromatography (eluting with 0-35% ethyl acetate in hexanes) to yield the product (71 mg, 50%). ESI-MS m/z calc. 484.12, found 485.0 (M+l)+. Retention time 2.17 minutes.

References: [1]Patent: WO2008/141119,2008,A2 .Location in patent: Page/Page column 149-150.

4
[ 1083168-94-8 ]
[ 893440-50-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen;Raney-Ni; In methanol; for 2.0h;	The mixture of 2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl) pyridine (300mg, 1 .1 mmol) and Raney-Ni(I Omg) in MeOH (10mL) was subject to H2 and stirred for 2h. After filtration, the filtrate was concentrated to give the title compound as a white solid (261 mg). Yield: 95.0%.
95%	With hydrogen; In methanol; for 2.0h;	The mixture of <strong>[1083168-94-8]2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine</strong> (300 mg, 1.1 mmol) and Raney-Ni (10 mg) in MeOH (10 mL) was subject to H2 and stirred for 2 h. After filtration, the filtrate was concentrated to give the title compound as a white solid (261 mg). Yield: 95.0%.
89%	With hydrogen;Raney-Ni; In methanol; at 20.0℃; for 2.0h;	To the solution of 2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan- 2-yl) pyridine (500 mg, 1 .79 mmol) in MeOH (50 ml_) was added Raney-Ni (50 mg). The reaction mixture was stirred at room temperature under H2 for 2h. Then the solid was filtered off, and the solvent was removed to afford 2-methoxy-5-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-3-amine in 89% yield (400 mg). m/z 251 (M+H)+.

89%

With hydrogen; In methanol; at 20.0℃; for 2.0h;

To the solution of <strong>[1083168-94-8]2-methoxy-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine</strong> (500 mg, 1.79 mmol) in MeOH (50 mL) was added Raney-Ni (50 mg). The reaction mixture was stirred at room temperature under H2 for 2 h. Then the solid was filtered off, and the solvent was removed to afford 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine in 89% yield (400 mg). m/z 251 (M+H)+.

References: [1]Patent: WO2012/34526,2012,A1 .Location in patent: Page/Page column 31-32.
[2]Patent: US2013/190307,2013,A1 .Location in patent: Paragraph 0151; 0152.
[3]Patent: WO2012/34526,2012,A1 .Location in patent: Page/Page column 33-34.
[4]Patent: US2013/190307,2013,A1 .Location in patent: Paragraph 0158; 0160.
[5]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 256 - 261.

5
[ 1083168-94-8 ]
[ 1083326-73-1 ]

References: [1]Patent: US2013/190307,2013,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 256 - 261.
[3]Patent: WO2012/34526,2012,A1 .

6
[ 1083168-94-8 ]
[ 1366050-38-5 ]

References: [1]Patent: US2013/190307,2013,A1 .
[2]Patent: WO2012/34526,2012,A1 .

7
[ 1083168-94-8 ]
[ 1366050-66-9 ]

References: [1]Patent: US2013/190307,2013,A1 .
[2]Patent: WO2012/34526,2012,A1 .

8
[ 1083168-94-8 ]
[ 1366049-56-0 ]

References: [1]Patent: US2013/190307,2013,A1 .
[2]Patent: WO2012/34526,2012,A1 .

9
[ 1083168-94-8 ]
[ 1366050-21-6 ]

References: [1]Patent: US2013/190307,2013,A1 .
[2]Patent: WO2012/34526,2012,A1 .

10
[ 372198-69-1 ]
[ 1083168-94-8 ]
ethyl 6-(6-methoxy-5-nitropyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.5%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; caesium carbonate; In N,N-dimethyl-formamide; at 90.0℃; for 8.0h;Inert atmosphere;	A solution of the 5 (1.40 g, 5 mmol), ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate (1.34 g, 5 mmol), Pd(dppf)2Cl2 (0.18 g,0.25 mmol) and Cs2CO3 (3.26 g, 10 mmol) in DMF (30 ml) under anatmosphere of N2 was stirred at 90 C for 8 h. DMF was removedunder reduced pressure and the residue was purified through acolumn chromatography on silica with chloroform/methanol (V:V50:1) as a white solid (3.06 g, 89.5% yield). mp 217-219 C.1H NMR(400 MHz, CDCl3) delta 9.60 (s, 1H, Ar-H), 8.68 (d, J 2.4 Hz, 1H, Ar-H),8.52 (d, J 2.4 Hz, 1H, Ar-H), 8.37 (s, 1H, Ar-H), 7.92 (d, J 9.3 Hz,1H, Ar-H), 7.64 (dd, J 9.3, 1.8 Hz, 1H, Ar-H), 4.46 (q, J 7.1 Hz, 2H,CH2), 4.20 (s, 3H, CH3), 1.45 (t, J 7.1 Hz, 3H, CH3). ESI-MS: m/z343.2 [MH].

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

11
[ 1083168-94-8 ]
ethyl 6-(6-methoxy-5-(methylsulfonamido)pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

12
[ 1083168-94-8 ]
ethyl 6-(5-(butylsulfonamido)-6-methoxypyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

13
[ 1083168-94-8 ]
ethyl 6-(6-methoxy-5-(2,4-difluorobenzenesulfonylamino)pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

14
[ 1083168-94-8 ]
6-(6-methoxy-5-(2,4-difluorobenzenesulfonamido)pyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxylic acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

15
[ 1083168-94-8 ]
6-(6-methoxy-5-(2,4-difluorobenzenesulfonylamino)pyridin-3-yl)-N-(2-(dimethylamino)ethyl)imidazo[1,2-a]pyridine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

16
[ 1083168-94-8 ]
6-(6-methoxy-5-(2,4-difluorobenzenesulfonylamino)pyridin-3-yl)-N-(2-morpholinylethyl)imidazo[1,2-a] pyridine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

17
[ 1083168-94-8 ]
6-(6-methoxy-5-(2,4-difluorobenzenesulfonamido)pyridin-3-yl)-N-(3-morpholinylpropyl)imidazo[1,2-a] pyridine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

18
[ 1083168-94-8 ]
1-(6-(5-(2,4-difluorophenylsulfonamido)-6-methoxypyridin-3-yl)imidazo[1,2-a]pyridine-3-carbonyl)piperidin-4-yl benzoate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

19
[ 1083168-94-8 ]
C₂₅H₂₃F₂N₅O₅S [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

20
[ 1083168-94-8 ]
6-(5-(2,4-difluorophenylsulfonamido)-6-methoxypyridin-3-yl)-N-(pyridin-4-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

21
[ 1083168-94-8 ]
ethyl 6-(5-amino-6-methoxypyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxylate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 139,p. 95 - 106.

22
[ 1083168-94-8 ]
C₂₄H₂₁F₂N₅O₄S [ No CAS ]